If your work happens in chat, why are you hiring through interviews?
Experiments with chat-based hiring interviews
During 2020 then pandemic gave me the perfect excuse to expiment with chat-based hiring interviews for remote roles in Product Management, Engineering, and Design. Here’s the slightly updated writeup on the how and why, with some additional thoughts about AI and how trust has been eroding based on the ubiquiotous use of chatbots. Enjoy!
My day-to-day communication at work includes a lot of writing: Slack messages, Notion pages (now Confluence), GitHub issues and comments. To work successfully in a remote environment, the written word makes all the difference. How do you select for that?
At the time I worked at a SaaS startup with around 20 employees, in full scaling mode. We decided to insist on a presentation letter (well, email), and included a chat-based interview - both to see how the candidate writes in long(ish) form and interacts in chat. Spoiler alert: you are more biased than you think.
Accents, visuals, and what it means for diversity
Hiring remotely theoretically should be great for diversity - more people from more backgrounds can apply. Adding some extra effort in distributing the opportunity outside LinkedIn (which continues to be frustratingly location based), and suddenly there are people in the hiring pipeline who are different to yourself.
Unfortunately the human brain has developed the unpopular opinion that similarity is a great proxy to define how much it likes and trusts a given person. A similar background allows you to quickly establish rapport and to communicate based on shared cultural stories, the way you look, the way you talk. The interactions feel easy, and these positive emotions will colour the write-up after your first interaction.
And that’s exactly what you don’t want to happen in your first interview.
Levelling the playing field through a necessary skill
My first experience with chat interviews was during the hiring process at Automattic, who pioneered good remote work practices 10-15 years ago. At the time, the entire process was text-based, mimicking the day-to-day operations in a completely distributed company. Later, and at a different company, I wanted to bring this equalizer to our hiring process as well.
On the surface, video calls seem easier, quicker, more convenient. However, in my day-to-day work I don’t want to rely on calls for everything. It is much more valuable that someone knows how to express themselves in writing. If this is a skill that is important for how your company operates - then you need to include it into your selection process anyway. You can’t take it for granted.
Watching people put their thoughts into written words is fascinating. Writing seems so much more risky, even vulnerable. Your words will persist in that chat, someone might call you out, challenge you, disagree. Not everyone is comfortable having to commit to a statement and potentially negotiating the nuances later.
On the flipside, meeting via chat continues to be a great way to reduce anxiety for those who don’t feel comfortable in video calls. It helps mitigate the prejudice-trap when we first encounter someone who’s very different. Your brain can’t create an “OMG THEY ARE DIFFERENT” reaction, if the only thing that’s available is text, and maybe some gifs.
An accent you aren’t accustomed to? It doesn’t show in writing. A haircut that reminds you of hateful Miss Jones from first grade? Without the video, you just avoided an involuntary snap judgement.
And AI or not - you end up with a word-for-word transcript that you can either summarise or share with the next person in the hiring process.
Recommended tools for remote hiring chats
Back in 2020 we gave candidates the choice between Discord and LinkedIn chat. Today I would simply invite them as a single-channel guest to Slack, or us Discord if the company policies do not allow for that.
The reason? Depending on the privacy setting in LinkedIn you don’t get the `xyz is typing` information, and it’s surprisingly relevant to keep conversations flowing in chat.
Why I am complementing the chat with a video call
The questions during the chat interviews usually focus on the candidate’s story, their plans for the future, their ability to describe processes and past experiences. The zoom call that follows (usually on the same day) allows for some more relaxed banter, since it’s not “recorded”. This is the feedback from candidates on the chat + call experience:
I was super anxious this morning, but now I feel like I already know you a little and that makes it so much easier.
I did not realize how difficult it is to explain myself in writing. It really makes you think.
You using that gif made all the difference. It made you seem very human.
It’s weird. But it makes total sense.
The fact that I ended up combining both chat and zoom is based on long (and sometimes heated) conversations with one of the company’s co-founders. For him, creating a personal connection via video call (or ideally in person) is paramount. For me, making sure that someone can communicate in a remote-first environment is of highest importance. Combining both approaches in the first interaction started off as an experiment, a kind of compromise. And it worked surprisingly well, so by now I feel like it is the approach that serves us best.
Thoughts on AI, shadow workers, and remote contracts
Almost every week there’s another article with sinister pictures of programmers from specific countries infiltrating big tech in America for industry espionage. This articles then recommend specific tracking and zero-trust software, OR advocate for full Return-To-Office to track identities on site.
This might be a reasonable approach if you are (the size of) Google, Apple, or Microsoft. For your startup, scale-up, or even SME, the risk is a lot lower, and a lot easier to mitigate.
For someone (AI or a malicious agent) to be successful, they need you to see them as a resource, not as a human. As soon as you include human connection into your policies and processes, it becomes harder to infiltrate you. You don’t need an office for that:
Weekly or biweekly 1:1s between managers and direct reports - with video and conversations that create connections, not just dashboard updates.
Biweekly or monthly team meetings where colleagues interact with each other.
Quarterly or bi-annual team meetings where colleagues work together in person and share food and stories.
Slack (or whichever platform you choose) with non-work related channels where people can connect over related interests - and a commitment by managers to help facilitate those.
As AI advances, creating human touch points becomes more important than ever. Your company retreats aren’t a perk. They are a tool to mitigate risk.
In the meantime, writing is still the number one skill to create persistent documentaton - and a non-negotiable if you are operating asyncronously. So check for it early, and in realistic circumstances.